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Price, demand and travel trends for Chicago O'Hare Intl Airport to Caribbean Islands flights

Use KAYAK data on prices, travel dates, airlines and seasonal trends to compare options and book flights with more confidence.

Are flights from Chicago O'Hare Intl Airport to Caribbean Islands cheaper or more expensive than last year?

Fares from Chicago O'Hare Intl Airport to Caribbean Islands are about 9% higher than they were in November last year, averaging $680 round-trip.

What's the cheapest month to fly from Chicago O'Hare Intl Airport to Caribbean Islands?

January is typically the cheapest month to fly from Chicago O'Hare Intl Airport to Caribbean Islands, with round-trip fares averaging $573. December and November are usually the most expensive, averaging $729 and $698, respectively.

How do fares from Chicago O'Hare Intl Airport to Caribbean Islands vary by day of the week?

On average, Monday is the cheapest day to fly from Chicago O'Hare Intl Airport to Caribbean Islands and Saturday is the most expensive. Looking at the past 12 months of KAYAK data, it's 14% more expensive to fly on a Saturday compared to Monday.

What's the best time of day to fly from Chicago O'Hare Intl Airport to Caribbean Islands?

It's cheapest to fly to Caribbean Islands in the afternoon with average prices of $558. The morning is the most expensive time to fly, with average prices of $679.

What's the best time to book a flight from Chicago O'Hare Intl Airport to Caribbean Islands?

Book your flights 7 weeks before your trip. KAYAK data collected over the past 12 months shows that booking in this window can save you around 13% compared to booking at the last minute (within 2 weeks of departure).

Key details for Chicago O'Hare Intl Airport to Caribbean Islands flights

Low season

September
Beat the crowds with an average 44% drop in travelers.
The most popular month to fly with an average 42% increase in travelers.

Your Chicago O'Hare Intl Airport to Caribbean Islands flight questions, answered

Find helpful answers about this route, including flight times, airports, airlines and booking tips.

  • How much should I budget for a flight from Chicago O'Hare Intl Airport to Caribbean Islands?

    Over the past 12 months, round-trip fares from Chicago O'Hare Intl Airport to Caribbean Islands have typically cost between $480 and $858.

  • Which airlines fly nonstop from Chicago O'Hare Intl Airport to Caribbean Islands?

    Based on the flight schedule for the next 3 months, 3 airlines offer nonstop flights on this route:

    • United Airlines
    • American Airlines
    • Arajet

  • Is it cheaper to fly with a layover from Chicago O'Hare Intl Airport to Caribbean Islands?

    Yes, nonstop flights from Chicago O'Hare Intl Airport to Caribbean Islands average $633 over the past 12 months, but flights with a layover can cost less. The most affordable connecting airports are:

    • Punta Cana (PUJ) (avg. price $444)
    • Fort Lauderdale (FLL) (avg. price $455)
    • Boston Logan Intl (BOS) (avg. price $481)

  • How long is a flight from Chicago O'Hare Intl Airport to Caribbean Islands?

    Nonstop flights from Chicago O'Hare Intl Airport to Caribbean Islands take 4h 32m on average.

  • Which cabin classes are available from Chicago O'Hare Intl Airport to Caribbean Islands?

    On flights from Chicago O'Hare Intl Airport to Caribbean Islands you can book Economy Class, Premium Economy Class, Business Class or First Class.

  • What are some popular landmarks around Caribbean Islands?

    Caribbean Islands is home to many popular sights. KAYAK travelers' favorites include:

    • Viejo San Juan
    • Palm Beach
    • Eagle Beach
    • Puerto Rico Convention Center

  • What are the earliest and latest flights from Chicago O'Hare Intl Airport to Caribbean Islands?

    The earliest nonstop flight from Chicago O'Hare Intl Airport to Caribbean Islands departs at 4:20 am and the latest leaves at 11:38 am. Nonstop flights take about 4h 32m.

Your guide to booking Chicago O'Hare Intl Airport to Caribbean Islands flights

Get tips on when to book, when to fly and what to know before your trip.
  • If you can plan ahead, the sweet spot for booking your flight is 7 weeks before your trip. KAYAK data shows fares in this window are around 13% lower than last-minute bookings (made within 2 weeks of departure). Not ready to commit? Set a Price Alert and we'll let you know when prices change.
  • Flexible with your dates? Fly in January to save some money. It's typically the cheapest month on this route, while flights in December will cost you the most.
  • Fly out on a Monday to get the cheapest fares. Avoid Saturday flights, which are about 14% more expensive.
  • Start your trip in Punta Cana, the most popular destination in Caribbean Islands. From there, it's easy to continue on to other popular spots such as San Juan, Oranjestad and Nassau.

Reviews of the top 5 airlines serving from O'Hare Intl to Caribbean Islands

 
Need help choosing which airline to fly with from O'Hare Intl to Caribbean Islands? KAYAK airline reviews give an overall score for each airline based on loads of factors, including comfort, boarding, in-flight entertainment and more, to make your decision easier. See airline scores according to verified KAYAK customer reviews.
7.3
United AirlinesOverall score based on 10486 reviews
7.7Boarding
7.3Comfort
7.1Entertainment
6.7Food
8.1Crew
Airline reviews

Very uncomfortable and cramped seats. Everything else was okay, the crew members were nice but nothing was exceptional.

4.0 OkayKatherine, Nov 2026
Read more United Airlines reviews

Very uncomfortable and cramped seats. Everything else was okay, the crew members were nice but nothing was exceptional.

Waited on tarmac for approximately 15-25 minutes before taking off. When landing, the time it took to taxi to our gate was the also 15-25 minutes.

Connection times always good online, but not in reality when first leg is delayed (2 out of 2 times this trip).

It was good flight was smooth, little cold on the plane but other wise good.

Great flight and crew. Need more legroom and DO NOT allow seats to recline.

The guy in front of me was talking constantly, even when the pilot was making announcements. I found this very disrespectful to the pilot and to others.

We left 1.5 hours late due to a “maintenance” issue. Very poor communication as to when we would board & depart. The crew in First Class was uncharacteristically not friendly). Delay into Brussels cost me my connection to Rome so lost the entire first day of vacation ( had a 10:30am flight to Rome - ended up on a 6:55pm flight).

Everything was OK except the meals, that was overpriced chicken meat.

Miss My connection I had to take a flight from Indianapolis to Denver , then to san fransisco , sleep in sans fransisco en the flight to Los Cabos the next morning

The TVs on the plane were all broken and inoperable. No snacks or food were served. Plane was very old and uncomfortable.

Fort Lauderdale doesn't have Priority Security line so why was such option available for purchase? I need a refund back

1/2 full flight, nice and comfy flight. On time, good service

Both ways the people in the rear section of the plane were forced to check their carry on bags. I would understand this if the size and number of bags were not limited, but I do not understand why there is not room for one small overhead bag per person, even if the flight is full. I could watch the baggage handlers loading the extra luggage from my window and I’m pretty sure mine wouldn’t have survived undamaged, even though it is new and sturdy.

You sent me a confirmation yesterday for a flight reservation today that I never made. What is going on?????

Entertainment, clean plane and funny pilot over the intercom was excellent… however, gate agent was rude and was probably a Spirit employee before they went bankrupt… there were 3 flight attendants - 2 of them didn’t want to be there the other one was kind and nice… I want you to recognize how you have to compete with Delta or South West airlines or even American Airlines which would choose over you at any given day from here on out. Please treat people respectfully. If you hate working in this industry - go and work somewhere else. The flight was very empty and it shouldn’t be hard to crack a smile once in a while. Very disappointing… I remember flying Jet Blue back in the day from Dulles IAD to LAX and you guys were super cool and fancy and made flying fun again - truly elevated the experience. Don’t become the next most hated airline… you can do better . I want you to succeed…

Free wifi was almost impossible to get, kept dropping the connection

Not good - we boarded and taxied for an hour before they told us there were technical issues with the plane. They told us we were going to need to deplane, parked back at the gate but then didn’t tell us we didn’t have to anymore. There was just a lot of uncertainties with poor communication.

3.5 hour delay because of “mundane” mx issue. Aircraft had to be towed 3 times.

Overall great experience, though my screen for entertainment was not working and I could see that others were.

Plane was very comfortable,ore legroom, help yourself snack are so weren't disturbed by staff passing up and down cabin, gluten free food availability and really efficient and friendly staff . Boarding and good to time. Highly recommend t

All good. Flight crew was super friendly at the end of a long day

The food in first class has taken a big downturn

Flight was fine. Just delays leaving due to mechanical issues. But flight crew were kind and professional. Seats were spacious. American doesn't need to have 9 groups for boarding.

Both departure and return flights had mechanical delays. Their planes are antiquated resulting in a two hour flight taking almost four hours to complete.

Crew were helpful, pilot kept us informed about turbulence, snack choice was awesome!

It was one of the worst I have ever had. The plane was over booked, and I did not have a seat. When I questioned why because I had booked this weeks in advance. I was brushed off to be advised they are trying to find someone to give up their seat. Only to be advised I would be boarding last. I had priority boarding in group 1-4. When I asked why I had to be last because that is not what I paid for I was advised it doesn't matter you will get a seat. The ticket person was very rude and unprofessional. The gate changed several times and it was going from one area to another area far away from where we were at. I feel like I should have been compensated in some kind of way because of the way I was treated. The ticket agent acted like it was my fault that the plane was over booked. Not one time was I apologized to for this inconvenience.

We did not fly on American Airlines from Chicago to London. We were rebooked on British Airways (by American Airlines) and our luggage was left behind. A full day delay and lost luggage.

I have posted the comments in the first flight leg.

First class snacks - stewardess gave out multiples to everyone until there was almost no selection left when she got back to me last in first class cabin. Nothing left that I would eat.

My feedback from the trip to Columbia to Chicago was meant for Chicago to Denver.

Was charged for ticket, unable to check in online, made the line to speak to someone at the counter but was told I did not show up in the system as having a ticket to fly - even though I have the email with confirmation and credit card was charged. I could not purchase another ticket at the counter, only online which was not working. Ended up buying a flight on another airline at the airport. Called customer service to claim the cost of the original ticket, was told I showed up in their system as having a ticket but did not check-in or show up to board the flight. Currently pending review for refund via their customer service team, they were very nice and helpful over the phone despite the many glitches.

Do not book with this airline. Flights delayed over 3 hours and no explanation. They keep changing your itinerary every hour.

Awful. Not water, or chargers or space under the seats, the plane was very old and poor maintenance, seats really dirty, sticky, seats pockets with wires pinching your knees. Connection with no announcements, plane departed 1.30 hour earlier for an extra stop to refueling in Trinidad & Tobago. Even that we had a 3 hrs delay, seated in the plane in the runway.

Really bad. Uncommunicated stop in Trinidad & Tobago for refueling. Extra stop added 3 hours of discomfort without allowing off the seat. Not even water, or chargers or boarding groups.

Staff were unfriendly and rude. Was stuck on runway for 2 hours after arrival in Boston.

Horrible service. No communication from the crew as to why a 6 hour delay then cancellation

The food for sale on board has opportunity for improvement.

I paid extra for a comfortable seat in the second flight, but the plane didn't have those seats, the first one did

The Arajet person who greeted us initially was unhelpful & rude about the mandatory migration form which has to be completed digitally but the systems don’t work properly. The boarding gate was changed twice and initial boarding was delayed. Once on board we we had to wait an hour and a half before take off. It was hot and there was very little room for tall-ish people to fit their knees in. The crew were pleasant but working in a poor situation. The plane was delayed because we were waiting for people from a delayed interconnecting flight. Arajet must have known that before we were asked to board. Better information, decisions & communication were needed.

My seat was broken and the crew had to find me somewhere else to sit. The crew was extremely courteous about this

During the flight I suddenly felt very sick, and no one from the crew even tried to help me or check on my condition. They seemed completely indifferent and showed no concern for my well-being. I was very disappointed by the lack of care and compassion. I hope the airline improves its customer service and trains its crew to respond better when passengers need assistance.

Flight was canceled. Most upsetting was message from Kayak, stating that the flight was canceled and click with Kayak for details regarding rebook, refund details. THERE'S NO INFORMATION PROVIDED BY KAYAK EXCEPT THAT FLIGHT IS CANCELED. AND NOW THIS SURVEY TO FIND OUT HOW WAS THE FLIGHT !!!!!!!

Better than expected. Staff were friendly and nice on both flights.

Just know that everything, and I mean everything is “ala cart”. 60$ just to put something in the overhead bin. I will never fly Frontier again nor do I recommend them to anyone else.

Great for the price. No wifi or entertainment, but gate agents and crew were fantastic and we boarded quickly and left on time.

Our flight was canceled for no known reason. We weren’t told until we were checking in at 5:00 am. This was after our last flight with Frontier where we sat on the plane for three hours (not an exaggeration) before we took off because of a mechanical issue. We won’t be flying Frontier again.

I didn’t have enough time to catch my connecting flight and had to use a different Airline. I will be requesting a refund.

I brought a ticket and car rental through Travelocity. There was no where to add a KTN. So I thought i’d add it by looking up ticket on frontier website. I tried 3 times with the frontier chat bot to add my KTN it never updated my boarding pass. So then I tried showing up early to do it in person at the airport. The first employee update my ktn in the system and gave me a new boarding pass. I was sent back by tsa to join regular line. Then I was told to add my Ktn. It would cost me $25 extra. Given the length of the cue I did pay. Congratulations! BUT I will NEVER fly frontier again. Plus the plane was very old. It had actual ashtrays and old looking tray backs. Worst travel experience ever. Im warning my friends and family not to use frontier ever.

It was delayed 9 hours for operational reasons, despite the plane arriving to the airport on time.

Was just ok with over selling I guess. A lot of people in a short space and when we finally arrive i20 minutes, waiting to get out from the plain because we were waiting authorization for out boarding? Something like that.

More options for your flight to Caribbean Islands

Complete your trip to Caribbean Islands with a hotel stay or car rental